HCID 18186376, compound → HCID 18186382, compound

HRID 1358049Notes

Reaction equation

HRID 1358049 reaction equation
[N:1]1([C:7]2[CH:38]=[CH:37][C:10]([CH2:11][CH:12]3[C:21]4[C:16](=[CH:17][C:18]([O:22]CC5C=CC=CC=5)=[CH:19][CH:20]=4)[CH2:15][CH2:14][N:13]3[C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd]>[N:1]1([C:7]2[CH:38]=[CH:37][C:10]([CH2:11][CH:12]3[C:21]4[C:16](=[CH:17][C:18]([OH:22])=[CH:19][CH:20]=4)[CH2:15][CH2:14][N:13]3[C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 18186376HCID 18186376, compound

Product 1

HCID 18186382HCID 18186382, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumSolvent

Procedure

1-{4-(N-Piperidyl)benzyl}-2-(4-fluorophenyl}-6-phenylmethoxy-1,2,3,4-tetrahydroisoquinoline (0.25 g, 0.49 mmol) was treated with H2 in 10% Pd/C as described in Example 14.D to yield 1-{4-(N-piperidyl)benzyl}-2-(4-fluorophenyl}-1,2,3,4-tetrahydroisoquinoline-6-ol. Treatment of the free base with conc. HCl in ether produces a fine white solid. The precipitate is filtered and dried under high vacuum to yield the title compound. (0.096 g, 47% yield): m.p. 177-179° C. (dec.).

Sources & evidence

ORD record
ord-280a83450bb5406290674f81a868781b
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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